Haunted Chicago: 4 Eerie Spots to Visit This Halloween

October is Here, and So is Haunted Chicago

Every October, the celebration of All Hallows’ Eve looms at the end of the month, giving Halloween lovers everywhere something to look forward to. From planning costumes to throwing parties to planning activities with the kids, Halloween is a great time for families and adults alike.

One thing that attracts many Halloween lovers is the idea of a ghost hunt or a haunted tour, of heading out to scary sites that have reports of paranormal activity to see if anything spooky happens when they set foot on the grounds.

Chicago is one of the most popular cities in the country for paranormal activity, ghost hunting and reports of hauntings—that’s why we’ve compiled this list of some of the creepiest places in the city, so you can build your very own Haunted Chicago tour this October.

Located at North Dearborn and Ontario is this unmissable Romanesque Revival-style building, which was completed in the late 19th Century and soon served as the headquarters for the Chicago Historical Society when their original building burned down in the Great Chicago Fire of 1871.

Various organizations have called the granite structure home since the Society vacated the property, including the Loyal Order of Moose and the Works Progress Administration in the early-to-mid 1900s.

Beginning in the 1980s, the building served as the site of several nightclubs and attracted many patrons on reports of paranormal sightings and rumors of the building having served a makeshift morgue during the Eastland Disaster of 1915. Those rumors have been debunked by several Chicago historians, but the eerie look of the building, combined with its long history in Chicago, make it a favorite for ghost hunters and paranormal specialists.

Built in 1882, the building that now houses the Red Lion Pub sits across from the Biograph Theatre, where John Dillinger famously stopped in for a movie in July of 1934 and then was gunned down by Federal Agents in the street as he exited the building.

It is said the Pub was the hangout of numerous organized crime figures through the early-to-mid 1900s, particularly bookies and gamblers who used the building’s third-floor as the site of their activities. Many people are reported to have died in the building since it was constructed, and many of those ghosts are reported to wander the property to this day.

Featured on a 2010 episode of Ghost Hunters, the Old Milton School, which functioned as a grammar school for children until 1984, is the reported site of numerous hauntings and ghosts.

Legend has it that a young girl, a student at the school, was murdered by a janitor in the girls’ locker room at the school. The janitor reported admitted to the murder in a suicide note that was found with his body, but none of these events can be found in Alton newspapers of the decade.

Nonetheless, paranormal investigators report strong activity in the building, especially in the girls’ locker room where the ghost of the murder girl is said to roam.

The Congress Plaza is among the more luxurious hotels in the cities, but it’s also said to be among the most haunted. Some say the Congress was even the inspiration for the Stephen King story “1408.”

Built to accommodate visitors to Chicago during the World’s Fair over 120 years ago, the Congress was named as such until 1908. Some stories say that the Congress was home to Al Capone under a fake name for a period of time during his heyday, while others report that a worker who helped build the structure was accidentally crushed and was then buried in the walls.

While none of the reports of murder or suicide in the hotel can be confirmed, many guests and historians say that paranormal activity has occurred in the building while they were there.

Transportation for Your Chicago Ghost Tour

When frights are in heavy supply, one comfort for your evening of ghost hunting can be reliable transportation.

OML Worldwide offers luxury car service, late-model vehicles, and professional chauffeurs to handle each leg of your haunted tour of Chicago, no matter where it takes you or what (or who) you see while you’re there.

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About OML

For over 60 years, O’Hare-Midway Limousine Service (OML Worldwide) has been the premier luxury transportation provider for the greater Chicagoland area. We have grown from simple airport drop off and pickup service to the worldwide comprehensive transportation company that we are today. Whether you are traveling in the Chicago area or need car service on the global level, OML Worldwide can take care of you.